WO2007064085A1 - Composition cosmetique contenant des hydrolysats de l'icariine - Google Patents

Composition cosmetique contenant des hydrolysats de l'icariine Download PDF

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Publication number
WO2007064085A1
WO2007064085A1 PCT/KR2006/004448 KR2006004448W WO2007064085A1 WO 2007064085 A1 WO2007064085 A1 WO 2007064085A1 KR 2006004448 W KR2006004448 W KR 2006004448W WO 2007064085 A1 WO2007064085 A1 WO 2007064085A1
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Prior art keywords
icariin
genus
icariside
composition according
enzyme
Prior art date
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PCT/KR2006/004448
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English (en)
Inventor
Jun Seong Park
Ho Sik Rho
Duck Hee Kim
Ih Seop Chang
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Amorepacific Corporation
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Application filed by Amorepacific Corporation filed Critical Amorepacific Corporation
Priority to US12/095,654 priority Critical patent/US8394775B2/en
Priority to CN2006800447555A priority patent/CN101316573B/zh
Priority to JP2008543174A priority patent/JP5227181B2/ja
Publication of WO2007064085A1 publication Critical patent/WO2007064085A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • the present invention relates to a cosmetic composition containing hydrolysates of icariin, and more particularly, a cosmetic composition containing hydrolysates of icariin, including icaritin, icariside I and icariside II, in which the hydrolysates of icariin is prepared by a method comprising the steps of: (a) obtaining an extract from a plant containing icariin using water or an organic solvent; and (b) hydrolyzing the plant extract with an acid, a base, an enzyme or a microorganism producing the enzyme.
  • Plants of the Epimedium genus belonging to the Berberidaceae family are classified into three species of E. brevicornum, E. sagittatum and E. koreanum, as described in Chinese pharmacopoeia. It has been reported that the plants of the Epimedium genus comprise main components of flavonoid, alkaloid and lignan. Particularly, the herb medicine prepared by drying the whole plant except for the root of Epimedium koreanum Nakai is called Epimeii Herb and has been used for treatment of total paralysis and amnesia, and an aphrodisiac and analeptic agent.
  • oxygen free radical generated by various physical, chemical and environmental factors such as enzyme system and reductive metabolism in the body, chemicals, pollutants and photochemical reaction induces various diseases including cell aging or cancers by non-selective, irreversible destruction against lipid, cell constituting materials such as protein, sugar and DNA.
  • the oxygen free radical is a cause of many diseases since various peroxides in the body including lipid peroxides generated by peroxidization of lipid by the oxygen free radical bring about oxidative destruction of cells, leading various functional disorders.
  • anti-oxidants such as free radical scavengers capable of removing free radical or substances inhibiting formation of peroxides such free radical are expected to be inhibitants or therapeutic agents against aging and various diseases caused by these peroxides.
  • free radical scavengers capable of removing free radical or substances inhibiting formation of peroxides such free radical are expected to be inhibitants or therapeutic agents against aging and various diseases caused by these peroxides.
  • many materials derived from natural sources were studied. However, most of the materials derived from natural sources were used in a simple extract form and substances, to which the effect of the extract was attributed, were not clearly shown. The materials have been used in the cosmetic composition by experience and information by word of mouth.
  • the skin aging is largely classified according to its cause.
  • One is natural aging (Intrinsic aging), in which the structure and physiological functions of the skin are continuously degraded as one becomes older.
  • the other one that is extrinsic aging is caused by external stress accumulated such as solar rays.
  • ultraviolet rays (UV) among the sun beams are the main cause of aging.
  • UV rays ultraviolet rays
  • the stratum corneum is thickened and collagen and elastin are denatured, whereby the skin loses its elasticity. These collagen and elastin are controlled by many factors.
  • retinoids such as retinol and retinoic acid show improvement of elasticity (Dermatology therapy, 1998, 16, 357 to 364) and a protein fraction obtained from Leguminosae seeds showed increase in elasticity (US Patent No. 5,322,839).
  • these retinoids have defects that they may cause irritation when they are applied on the skin even in a small amount. They are mainly materials derived from natural materials and thus, it is not clarified that which components of the extract show the effect. Accordingly, it is difficult to maintain and control the activity of the extract.
  • melanin a black pigment, produced by action of various enzymes such as tyrosinase in melanocyte of the human body.
  • the formation of this melanin pigment is affected by genetic factors, physiological factors associated with hormone secretion and stress and environmental factors such as irradiation of UV rays.
  • the melanin pigment generated in melanin cells of the human skin is a high-molecular weight phenolic compound having a composite structure of a black pigment and a protein and intercepts UV rays from the sun to protect skin organisms under the dermis while protecting proteins and genes in the skin by capturing free radicals produced in the skin.
  • melanin generated by the external stress stimulation is a stable substance which does not disappear, even when the stress is released, until it is discharged through keratinization of the skin.
  • cosmetically undesirable conditions such as discoloration, freckles or speckles may be induced.
  • icariin which is a flavonoidic component in the extract of plants belonging to the Epimedium genus, has those effects and hydrolysates of icariin prepared by hydrolyzing icariin using an acid, a base, an enzyme or a microorganism producing the enzyme are more excellent in anti-oxidant, anti-aging and whitening effects.
  • Rl is OH or rhamnopyranose
  • R2 is OH or glucopyranose, provided that both Rl and R2 are not rhamnopyranose or glucopyranose at the same time.
  • the composition is a cosmetic composition for anti-oxidant, anti-aging, whitening or anti- wrinkle effects.
  • the hydrolysates of icariin contained in the cosmetic composition according to the present invention is prepared by a method comprising the steps of: (a) obtaining an extract from a plant containing icariin using water or an organic solvent; and (b) hydrolyzing the plant extract with an acid, a base, an enzyme or a microorganism producing the enzyme.
  • the extract in the step (a) is extracted from a plant belonging to the
  • Epimedium genus and the organic solvent may be at least one selected from the group consisting of ethanol, methanol, butanol, ether, ethylacetate and chloroform, or a mixture thereof with water, with preference being 80% ethanol.
  • the acid used in the step (b) may be at least one selected from the group consisting of hydrochloric acid, sulphuric acid, and nitric acid, or a mixture thereof with at least one selected from the group consisting of ethanol, methanol and butanol.
  • the concentration of the acid is 0.1 to 2 N and the content of the alcohol in the alcoholic solvent mixture is 10 to 50%.
  • the reaction temperature is 50 to 100 ° C and the reaction time is 0.5 to 8 hours.
  • the base used in the step (b) may be at least one selected from the group consisting of sodium hydroxide and potassium hydroxide, or a mixture thereof with at least one selected from the group consisting of ethanol, methanol and butanol.
  • the concentration of the base is 0.1 to 2 N and the content of the alcohol in the alcoholic solvent mixture is 10 to 50%.
  • the reaction temperature is 50 to 100 ° C and the reaction time is 0.5 to 24 hours.
  • the enzyme or the microorganism producing the enzyme used in the step (b) may be an enzyme decomposing a sugar linkage or a microorganism producing the enzyme decomposing a sugar linkage.
  • the enzyme removes the sugar part in icariin to produce hydrolysates of icariin.
  • the enzyme may be at least one selected from the group consisting of glucosidase, arabinosidase, rhamnosidase, xylosidase, cellulase, hesperidinase, naringinase, glucuronidase, pectinase, galactosidase and amyloglucosidase.
  • the microorganism producing the enzyme may be at least one selected from the group consisting of Aspergillus genus, Bacillus genus, Penicillium genus, Rhizopus genus, Rhizomucor genus, Talaromyces genus, Bifidobacterium genus, Mortierella genus, Cryptococcus genus and Microbacterium genus. [Best Mode]
  • icariin and hydrolysates of icariin that is, icaritin, icarisides I and II have the following formula: [Formula 1 ]
  • the following method for obtaining a plant extract containing icariin with water or an organic solvent from the plant is performed.
  • the plant is put into about 1 to 6 folds, preferably about 3 folds of water, or at least one organic solvent selected from the group consisting of ethanol, methanol, butanol, ether, ethylacetate and chloroform or a mixture thereof with water, stirred 1 to 5 times at room temperature and defatted.
  • the defatted plant is then put into about to 8 folds, preferably about 4 folds water or an organic solvent, extracted 1 to 5 times under reflux and settled for 1 to 3 days at 10 to 20 ° C.
  • the settled is separated into residue and filtrate through filtration and centrifugation.
  • the filtrate is concentrated under pressure to obtain the extract.
  • the extract is suspended in water and decolorized with ether.
  • the water layer is extracted off 1 to 5 times with butanol and the resulting organic solvent layer is concentrated under pressure to obtain the butanol extract.
  • the butanol extract is taken into a small mount of methanol and mixed with a large amount of ethylacetate. The resulting precipitation is dried to give icariin.
  • icariin obtained from the step (a) is hydrolyzed with an acid, a base, an enzyme or a microorganism producing the enzyme to produce hydrolysates of icariin.
  • the plant extract is mixed with an acid or a mixture of an acid and an alcohol, preferably 50% ethanol mixture, at a concentration of 0.1 to 2 N, preferably 1 N, and heated to reflux in a water bath at 50 to 100 ° C, preferably 80 °C, for 1 to 48 hours, preferably 8 hours, to obtain the reactant.
  • an acid or a mixture of an acid and an alcohol preferably 50% ethanol mixture
  • the plant extract is mixed with a base or a mixture of a base and an alcohol, preferably 50% butanol mixture, at a concentration of 0.1 to 2 N, preferably IN, and heated to reflux in a water bath at 50 to 100 ° C, preferably 100 ° C, for 1 to 48 hours, preferably 8 hours, to obtain the reactant.
  • a base or a mixture of a base and an alcohol preferably 50% butanol mixture
  • the plant extract is dissolved in 5 to 20 folds, preferably about 10 folds of an acid buffer solution.
  • the enzyme is added to the solution and stirred in a water bath at about 37 " C for about 40 to 55 hours, preferably about 48 hours.
  • the hydrolysis reaction is finished by heating in hot water (80 to 100 0 C) for 5 to 15 minutes to obtain the reactant.
  • the plant extract is dissolved in 5 to 10 folds, preferably about 10 folds of ionized water, sterilized at about 121 ° C for 30 minutes, cooled to about 30 ° C, inoculated with a microorganism, which has been cultured, in an amount of 5 to 10% based of the total amount of the solution and cultivated at 30 0 C for 2 to 5 days, preferably 5 days.
  • the hydrolysis reaction is finished by heating in hot water (80 to 100 " C) for 5 to 15 minutes.
  • the resulting culture fluid is centrifuged at 5,000 to 10,000 rpm.
  • the precipitation is washed 3 times with distilled water and centrifuged to obtain precipitation as the reactant.
  • the reactant obtained by hydrolysis with an acid, a base, an enzyme or a microorganism producing the enzyme as described above is concentrated under pressure to remove the solvent.
  • the residue is added to an alcohol, stirred 1 to 5 times.
  • the hydrolysates of icariin prepared according to the present invention has excellent anti-oxidant effect by inhibition of DPPH and ROS formation, anti-aging effect by promotion of collagen biosynthesis and inhibition of collagenase expression and whitening effect by inhibition of melanin production and improvement of pigmentation caused by UV rays.
  • a cosmetic composition for anti-oxidant effect comprising the hydrolysates of icariin as an effective ingredient. Also, according to the present invention, there is provided a cosmetic composition for anti-aging effect comprising the hydrolysates of icariin as an effective ingredient.
  • a cosmetic composition for whitening effect comprising the hydrolysates of icariin as an effective ingredient.
  • a cosmetic composition for wrinkle improving effect comprising the hydrolysates of icariin as an effective ingredient.
  • the cosmetic composition may be formulated into a cosmetic composition or a pharmaceutical composition and the content of the hydrolysates of icariin in the composition is in the range of 0.0001 to 10 wt% based on the total weight of the composition.
  • the composition may comprise one or more of the hydrolysates of icariin.
  • Acid hydrolysates icaritin, glucose, rhamnose
  • Acid hydroly sates icaritin, glucose
  • Acid hydroly sates icaritin, rhamnose
  • a method for evaluating anti-oxidant effect through change of absorption generated by reduction of the organic radical DPPH(1, 1-diphenyl- 2-picryl hydrazyl)(while anti-oxidant is oxidized) is used.
  • icaritin, icarisides I and II according to the present invention showed better activity than icariin and even better antioxidant effect than Trolox.
  • HCSS HPES-buffered control salt solution
  • icaritin, icarisides I and II according to the present invention showed better activity than icariin and even better inhibition effect on ROS production than Trolox.
  • icaritin, icarisides I and II according to the present invention showed greater increase of collagen biosynthesis than icariin and even better effect than the positive control.
  • human fibroblasts were seeded in a 96-well microtiter plate containing DMEM supplemented with 2.5% fetal bovine serum at a level of 5000 cells per well and cultured until they grew up to 90%.
  • the cells were cultured in serum free DMEM for 24 hours, treated with icariin, icariside I 5 icariside II and icaritin, identified in Examples 1 to 2; tocopherol and EGCG, as test materials, dissolved in serum free DMEM medium at a molar concentration of 10 "4 and cultivated for 24 hours to take culture fluid.
  • the culture fluid was examined for formation of collagenase using a commercially available collagenase measuring kit (Amorsham pharmacia, USA).
  • the taken cell culture fluid was added to the 96-well plate having the primary collagenase antibody evenly applied and left for antigen- antibody reaction in a thermostat for 3 hours. After 3 hours, the secondary collagen antibody having a chromophore bonded thereto was added to the 96- well plate and left for reaction for 15 minutes. After 15 minutes, a color developing agent was added and left for 15 minutes. Then, IM sulphuric acid was added to quit the reaction (color development), upon which the color of the reaction became yellow. The yellow level varied according to the progress of the reaction.
  • human fibroblasts were seeded in a 96-well microtiter plate containing DMEM supplemented with 2.5% fetal bovine serum at a level of 5000 cells per well and cultured until they grew up to 90%.
  • the cells were cultured in serum free medium for 24 hours, treated with icariin, icariside I, icariside II and icaritin, identified in Examples 1 to 2,; tocopherol and EGCG, as test materials, dissolved in serum free DMEM medium at a molar concentration of 10 "4 and cultivated for 24 hours to take culture fluid.
  • the culture fluid was examined for formation of elastase using a commercially available elastase measuring kit (Amorsham pharmacia, USA).
  • the taken cell culture fluid was added to the 96-well plate having the primary elastase antibody evenly applied and left for antigen- antibody reaction in a thermostat for 3 hours. After 3 hours, the secondary collagen antibody having a chromophore bonded thereto was added to the 96- well plate and left for reaction for 15 minutes. After 15 minutes, a color developing agent was added and left for 15 minutes. Then, IM sulphuric acid was added to quit the reaction (color development), upon which the color of the reaction became yellow. The yellow level varied according to the progress of the reaction.
  • pigment cells of mouse were used. Firstly, pigment cells (MeI-Ab cell) of rat derived from C57BL/6 mouse (Dooley, T.P. et al, Skin pharmacol, 7, pp 188-200) were cultured in
  • MeI-Ab cells were separated with 0.25% trypsin-EDTA and cultured in a 24-well plate at a concentration 10 5 (cells /well). After 2 days,
  • hydroquinone 10 ppm of respective test materials of hydroquinone, icariin, icariside I, icariside II and icaritin, identified in Examples 1 and 2 were added for continuous 3 days and cultivated.
  • hydroquinone was a positive control.
  • the culture fluid was removed and washed with PBS.
  • the cells were lysed with IN sodium hydroxide and absorption was measured 400nm.
  • the inhibition rate of melanin synthesis was calculated according to the following
  • Equation III Equation III and the result is shown in Table 6 (Dooley 's method).
  • Example 1 Particularly, icaritin, icarisides I and II showed a similar inhibition effect on melanin synthesis to hydroquinone.
  • the difference of skin color ( ⁇ L*) between the point when the application of the test material was initiated and the point when the application of the test material was completed was calculated according to the following equation and the result is shown in Table 7. Meanwhile, the whitening effect was determined by comparison of ⁇ L* between the sample applied part and the control. When ⁇ L* value is about 2, the whitening of the pigmentation was significant. When ⁇ L* is over 1.5, it was considered that the sample had whitening effect.
  • the icariin, icariside I, icariside II and icaritin prepared in Examples 1 to 2 according to the present invention showed brightness of skin similar to hydroquinone. It is because the above materials improved the pigmentation caused by UV rays and brightened the skin color.
  • the ingredients in the described mixing ratio were compounded with purified water to make the total weight of 100.
  • the ingredients were mixed in the above-described mixing ratio and purified water was added to make 100 of the total weight.
  • the ingredients were mixed in the above-described mixing ratio and purified water was added to make 100 of the total weight.
  • the ingredients were mixed in the above-described mixing ratio and purified water was added to make 100 of the total weight.
  • the ingredients were mixed in the above-described mixing ratio and purified water was added to make 100 of the total weight.
  • the ingredients were compounded according to a commonly used method for preparing capsules and filled into gelatin capsules.
  • the ingredients were dissolved in purified water according to a commonly used method for preparing a solution. After lemon incense was added, the ingredients were mixed and purified water added to the mixture to make the total volume of 100 ml. The resulting solution was then filled into an amber bottle. [ Industrial Applicability ]
  • the cosmetic composition containing hydrolysates of icariin which is prepared by hydrolyzing icarrin, a flavonoid ingredient in an extract from a plant of the Epimedium genus, with an acid, a base, an enzyme or a microorganism producing the enzyme, has anti-oxidant effect to inhibit production of DPPH and ROS, anti-aging effect by promotion of collagen biosynthesis, inhibition of expresseion of elastase and collagenase, and whitening effect by inhibition of melanin production and improvement of pigmentation caused by ultraviolet rays (UV). Therefore, the hydrolysates of icariin according to the present invention may be usefully used as a cosmetic composition or a pharmaceutical composition for anti-oxidant, anti-aging, whitening and anti- wrinkle effects.

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Abstract

La présente invention porte sur une composition cosmétique contenant des hydrolysats de l'icariine, et plus particulièrement, sur une composition cosmétique contenant des hydrolysats de l'icariine comprenant l'icaritine, l'icariside I et l'icariside II. Pour préparer les hydrolysats de l'cariine, on utilise un procédé consistant à: (a) obtenir un extrait d'une plante contenant l'icariine au moyen d'eau ou d'un solvant organique; et (b) hydrolyser l'extrait de plante avec un acide, une base, une enzyme ou un micro-organisme produisant l'enzyme. La composition cosmétique de l'invention est utilisée pour obtenir des effets antioxydants, antivieillissement, de blanchiment ou antirides.
PCT/KR2006/004448 2005-11-30 2006-10-30 Composition cosmetique contenant des hydrolysats de l'icariine WO2007064085A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US12/095,654 US8394775B2 (en) 2005-11-30 2006-10-30 Cosmetic composition containing hydrolysates of icariin
CN2006800447555A CN101316573B (zh) 2005-11-30 2006-10-30 一种含有淫羊藿苷的水解产物的化妆品组合物
JP2008543174A JP5227181B2 (ja) 2005-11-30 2006-10-30 イカリイン加水分解物を含有する化粧料用組成物

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KR1020050115649A KR100803577B1 (ko) 2005-11-30 2005-11-30 이카린의 가수분해물을 함유하는 화장료용 조성물
KR10-2005-0115649 2005-11-30

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WO2009149621A1 (fr) * 2008-06-13 2009-12-17 北京东方百奥医药开发有限公司 Utilisation de l’icariside ii dans la fabrication de produits pour prévenir ou traiter un dysfonctionnement sexuel masculin ou féminin
EP2623108A1 (fr) * 2010-09-28 2013-08-07 Korea Institute of Oriental Medicine Composition utilisée pour la prévention ou le traitement d'une dermatite atopique, comprenant un extrait galénique ou une fermentation par lactobacille de ce dernier
EP2332946B1 (fr) * 2009-12-10 2015-07-08 Evonik Degussa GmbH Agent de séparation et utilisation pour la fabrication de corps moulés composites
CN107964555A (zh) * 2018-01-05 2018-04-27 苏州广奥医药开发有限公司 一种生物富集并生产淫羊藿次苷ⅱ的方法
CN110699263A (zh) * 2019-10-29 2020-01-17 浙江工业大学 黑曲霉yh-6及其应用于提高淫羊藿中淫羊藿素的含量
AU2017282545B2 (en) * 2016-06-24 2022-04-14 Suntory Holdings Limited Composition for browning inhibition and use of same

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KR20080025960A (ko) * 2006-09-19 2008-03-24 (주)아모레퍼시픽 이카리시드 ⅰⅰ의 제조 방법 및 이를 함유하는 미백용조성물
JP5300233B2 (ja) * 2007-09-14 2013-09-25 丸善製薬株式会社 皮膚化粧料
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KR101040477B1 (ko) * 2008-06-03 2011-06-09 고려대학교 산학협력단 항안드로겐 조성물
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JP2011046646A (ja) * 2009-08-27 2011-03-10 Noevir Co Ltd 抗酸化剤及び皮膚外用剤
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